Quick facts:
HQ: Chicago, IL, United States
Incorporated: 2025
Funding:
$795K · Equity · Oct 2026
Top Startups in Chicago
This list has 51 startups and was last updated on Oct 15, 2026. 6 of them are hiring right now. Largest teams: Tovala, Vouch, and Zerocater. Latest round: Factron AI raised $250K (Oct 5, 2026).
51 startupsPage 2 of 2
Quick facts:
HQ: Chicago, IL, United States
Incorporated: 2025
Funding:
$250K · SAFE · Oct 2026
Obie
Acquired
What they do:
Moving Investment Property Insurance Forward
Quick facts:
HQ: Chicago, IL, United States
Bluecrew
Acquired
What they do:
Bluecrew is a web based staffing agency.
Quick facts:
HQ: Chicago, IL, United States
Popular Pays
Acquired
What they do:
Software for collaborating with content creators and influencers
Quick facts:
HQ: Chicago, IL, United States
Aisle50
Acquired
What they do:
Grocery deals.
Quick facts:
HQ: Chicago, IL, United States
Inkling
Acquired
What they do:
Inkling, based in Chicago, Illinois, offers collective intelligence solutions to help organizations make more informed decisions. Inkling's products have been…
Quick facts:
HQ: Chicago, IL, United States
TaxProper
Acquired
What they do:
TaxProper helps large Real Estate owners manage their property taxes.
Quick facts:
HQ: Chicago, IL, United States
Preflight
Acquired
What they do:
No-code Web Apps testing for everyone
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HQ: Chicago, IL, United States
Debteye
Acquired
What they do:
Automate credit counseling.
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HQ: Chicago, IL, United States
Tutorspree
Shut down
What they do:
Online tutoring marketplace.
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HQ: Chicago, IL, United States
Charge Running
Shut down
What they do:
Provides live, virtual running classes to runners all around the world
Quick facts:
HQ: Chicago, IL, United States
TRAC
Shut down
What they do:
An end to end timing solution for any scale athletic event.
Quick facts:
HQ: Chicago, IL, United States
Draft
Shut down
What they do:
Making Draft. Super simple version control and collaboration for…
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HQ: Chicago, IL, United States
Protobase
Shut down
What they do:
Protobase is a 10x, next-generation spreadsheet.
Quick facts:
HQ: Chicago, IL, United States